CA2285516C - Agents d'imagerie pour transporteur de dopamine - Google Patents
Agents d'imagerie pour transporteur de dopamine Download PDFInfo
- Publication number
- CA2285516C CA2285516C CA2285516A CA2285516A CA2285516C CA 2285516 C CA2285516 C CA 2285516C CA 2285516 A CA2285516 A CA 2285516A CA 2285516 A CA2285516 A CA 2285516A CA 2285516 C CA2285516 C CA 2285516C
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- CA
- Canada
- Prior art keywords
- compound
- mmol
- etoac
- tropane
- et3n
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 102000006441 Dopamine Plasma Membrane Transport Proteins Human genes 0.000 title abstract description 58
- 108010044266 Dopamine Plasma Membrane Transport Proteins Proteins 0.000 title abstract description 58
- 239000012216 imaging agent Substances 0.000 title description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 102
- 229930004006 tropane Natural products 0.000 claims abstract description 32
- XLRPYZSEQKXZAA-OCAPTIKFSA-N tropane Chemical compound C1CC[C@H]2CC[C@@H]1N2C XLRPYZSEQKXZAA-OCAPTIKFSA-N 0.000 claims description 28
- DGGKXQQCVPAUEA-UHFFFAOYSA-N 8-azabicyclo[3.2.1]octane Chemical compound C1CCC2CCC1N2 DGGKXQQCVPAUEA-UHFFFAOYSA-N 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- -1 tropane compound Chemical class 0.000 abstract description 89
- 229910052713 technetium Inorganic materials 0.000 abstract description 47
- 229910052702 rhenium Inorganic materials 0.000 abstract description 43
- 239000003446 ligand Substances 0.000 abstract description 41
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 abstract description 37
- GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 abstract description 36
- 239000000203 mixture Substances 0.000 abstract description 27
- 239000012217 radiopharmaceutical Substances 0.000 abstract description 25
- 229940121896 radiopharmaceutical Drugs 0.000 abstract description 25
- 230000002799 radiopharmaceutical effect Effects 0.000 abstract description 25
- 102000019208 Serotonin Plasma Membrane Transport Proteins Human genes 0.000 abstract description 16
- 108010012996 Serotonin Plasma Membrane Transport Proteins Proteins 0.000 abstract description 16
- 230000007935 neutral effect Effects 0.000 abstract description 7
- 230000000536 complexating effect Effects 0.000 abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 295
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 220
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 167
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 127
- 235000019439 ethyl acetate Nutrition 0.000 description 109
- 239000000243 solution Substances 0.000 description 109
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 70
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- 101150041968 CDC13 gene Proteins 0.000 description 67
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 67
- 238000005160 1H NMR spectroscopy Methods 0.000 description 63
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 54
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 50
- 238000010992 reflux Methods 0.000 description 44
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 39
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- 239000007832 Na2SO4 Substances 0.000 description 38
- 239000000047 product Substances 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 34
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 33
- 238000000921 elemental analysis Methods 0.000 description 32
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 30
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- 239000000377 silicon dioxide Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 25
- 235000011114 ammonium hydroxide Nutrition 0.000 description 25
- 239000000284 extract Substances 0.000 description 24
- 241001446467 Mama Species 0.000 description 23
- 210000004556 brain Anatomy 0.000 description 23
- 229910052681 coesite Inorganic materials 0.000 description 23
- 229910052906 cristobalite Inorganic materials 0.000 description 23
- 239000002904 solvent Substances 0.000 description 23
- 229910052682 stishovite Inorganic materials 0.000 description 23
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- 239000007787 solid Substances 0.000 description 22
- 239000003480 eluent Substances 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- QOPVNWQGBQYBBP-UHFFFAOYSA-N chloroethyl chloroformate Chemical compound CC(Cl)OC(Cl)=O QOPVNWQGBQYBBP-UHFFFAOYSA-N 0.000 description 20
- 238000004587 chromatography analysis Methods 0.000 description 20
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 20
- 239000006260 foam Substances 0.000 description 20
- 230000002829 reductive effect Effects 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 18
- 235000012239 silicon dioxide Nutrition 0.000 description 18
- 238000000034 method Methods 0.000 description 17
- 210000001577 neostriatum Anatomy 0.000 description 17
- 235000017557 sodium bicarbonate Nutrition 0.000 description 17
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 230000027455 binding Effects 0.000 description 16
- 238000002329 infrared spectrum Methods 0.000 description 16
- 239000003921 oil Substances 0.000 description 16
- 229910000027 potassium carbonate Inorganic materials 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- 238000003384 imaging method Methods 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- 238000004440 column chromatography Methods 0.000 description 14
- 238000003818 flash chromatography Methods 0.000 description 14
- 238000002347 injection Methods 0.000 description 14
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- 229910052757 nitrogen Inorganic materials 0.000 description 14
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 12
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- 238000002603 single-photon emission computed tomography Methods 0.000 description 12
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- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 10
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 10
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- 229960003638 dopamine Drugs 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- 238000011282 treatment Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
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- 239000011734 sodium Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- PLRACCBDVIHHLZ-UHFFFAOYSA-N 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine Chemical compound C1N(C)CCC(C=2C=CC=CC=2)=C1 PLRACCBDVIHHLZ-UHFFFAOYSA-N 0.000 description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
- 101001135571 Mus musculus Tyrosine-protein phosphatase non-receptor type 2 Proteins 0.000 description 7
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- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
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- BHKPQZVLIZKSAG-UHFFFAOYSA-N 2-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-4,5-diethyl-1,2,4-triazol-3-one;hydron;chloride Chemical compound Cl.O=C1N(CC)C(CC)=NN1CCCN1CCN(C=2C=C(Cl)C=CC=2)CC1 BHKPQZVLIZKSAG-UHFFFAOYSA-N 0.000 description 5
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- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000009206 nuclear medicine Methods 0.000 description 1
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- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 208000000170 postencephalitic Parkinson disease Diseases 0.000 description 1
- 230000001144 postural effect Effects 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 210000002637 putamen Anatomy 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 230000005258 radioactive decay Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
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- 238000010244 region-of-interest analysis Methods 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- SIIICDNNMDMWCI-YJNKXOJESA-N rti-55 Chemical compound C1([C@H]2C[C@@H]3CC[C@@H](N3C)[C@H]2C(=O)OC)=CC=C(I)C=C1 SIIICDNNMDMWCI-YJNKXOJESA-N 0.000 description 1
- UAWABSHMGXMCRK-UHFFFAOYSA-L samarium(ii) iodide Chemical compound I[Sm]I UAWABSHMGXMCRK-UHFFFAOYSA-L 0.000 description 1
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- 229940076279 serotonin Drugs 0.000 description 1
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- 238000010561 standard procedure Methods 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
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- 210000001550 testis Anatomy 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- QXTIBZLKQPJVII-UHFFFAOYSA-N triethylsilicon Chemical compound CC[Si](CC)CC QXTIBZLKQPJVII-UHFFFAOYSA-N 0.000 description 1
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
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- BPICBUSOMSTKRF-UHFFFAOYSA-N xylazine Chemical compound CC1=CC=CC(C)=C1NC1=NCCCS1 BPICBUSOMSTKRF-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/46—8-Azabicyclo [3.2.1] octane; Derivatives thereof, e.g. atropine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/041—Heterocyclic compounds
- A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
- A61K51/0446—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K51/0448—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil tropane or nortropane groups, e.g. cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0474—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group
- A61K51/0478—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group complexes from non-cyclic ligands, e.g. EDTA, MAG3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0497—Organic compounds conjugates with a carrier being an organic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
- C07F13/005—Compounds without a metal-carbon linkage
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
- A61B6/00—Apparatus or devices for radiation diagnosis; Apparatus or devices for radiation diagnosis combined with radiation therapy equipment
- A61B6/50—Apparatus or devices for radiation diagnosis; Apparatus or devices for radiation diagnosis combined with radiation therapy equipment specially adapted for specific body parts; specially adapted for specific clinical applications
- A61B6/506—Apparatus or devices for radiation diagnosis; Apparatus or devices for radiation diagnosis combined with radiation therapy equipment specially adapted for specific body parts; specially adapted for specific clinical applications for diagnosis of nerves
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Emergency Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2721484A CA2721484A1 (fr) | 1999-05-12 | 1999-10-01 | Agents d'imagerie pour transporteur de dopamine |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13376199P | 1999-05-12 | 1999-05-12 | |
| US60/133,761 | 1999-05-12 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2721484A Division CA2721484A1 (fr) | 1999-05-12 | 1999-10-01 | Agents d'imagerie pour transporteur de dopamine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2285516A1 CA2285516A1 (fr) | 2000-11-12 |
| CA2285516C true CA2285516C (fr) | 2010-12-07 |
Family
ID=22460191
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2285516A Expired - Fee Related CA2285516C (fr) | 1999-05-12 | 1999-10-01 | Agents d'imagerie pour transporteur de dopamine |
| CA2721484A Abandoned CA2721484A1 (fr) | 1999-05-12 | 1999-10-01 | Agents d'imagerie pour transporteur de dopamine |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2721484A Abandoned CA2721484A1 (fr) | 1999-05-12 | 1999-10-01 | Agents d'imagerie pour transporteur de dopamine |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US6548041B1 (fr) |
| EP (4) | EP1238978A3 (fr) |
| JP (3) | JP5001480B2 (fr) |
| KR (1) | KR20000075416A (fr) |
| AU (2) | AU783860B2 (fr) |
| CA (2) | CA2285516C (fr) |
| DE (2) | DE29923477U1 (fr) |
| GB (1) | GB2349882B (fr) |
| IL (1) | IL132488A0 (fr) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2285516C (fr) * | 1999-05-12 | 2010-12-07 | President And Fellows Of Harvard College | Agents d'imagerie pour transporteur de dopamine |
| US7553478B2 (en) * | 1999-05-12 | 2009-06-30 | President And Fellows Of Harvard College | Methods for diagnosing and monitoring treatment ADHD by assessing the dopamine transporter level |
| US20100143248A1 (en) * | 1999-06-28 | 2010-06-10 | President And Fellows Of Harvard College | Methods for diagnosing and monitoring treatment of adhd by assessing the dopamine transporter level |
| DE20120708U1 (de) | 2001-10-09 | 2002-08-01 | Meltzer Peter C | Tropan-Analoga zur Inhibierung des Monoamin-Transports |
| FR2833952B1 (fr) * | 2001-12-26 | 2004-03-26 | Schering Ag | Derive du tropane, produit de chelation comprenant ce derive de tropane et un metal ou un complexe de metal et radiopharmaceutique |
| JP2005527495A (ja) | 2002-02-08 | 2005-09-15 | プレジデント・アンド・フェロウズ・オブ・ハーバード・カレッジ | 治療化合物 |
| CA2505529C (fr) * | 2002-11-08 | 2013-12-24 | President And Fellows Of Harvard College | Petits agents marques au technetium-99 et au rhenium, et procedes pour representer en images des tissus, des organes et des tumeurs |
| US8084018B2 (en) * | 2007-10-31 | 2011-12-27 | Alseres Pharmaceuticals, Inc. | Methods for imaging dopamine transporter level |
| JP2011500857A (ja) | 2007-10-31 | 2011-01-06 | アルセレス ファーマシューティカルズ， インコーポレイテッド | 標識ヨウ化トロパン処方物 |
| WO2009114742A2 (fr) * | 2008-03-12 | 2009-09-17 | Organix, Inc. | Composés bisthiol stables pour la radio-imagerie et la radiothérapie |
| AU2014326601B2 (en) * | 2013-09-25 | 2018-01-18 | SpecGx LLC | Preparation of radioiodinated 3-fluoropropyl-nor-beta-CIT |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US476505A (en) * | 1892-06-07 | Frederick k | ||
| US3813404A (en) * | 1972-11-15 | 1974-05-28 | Sterling Drug Inc | Tropane-2-carboxylates and derivatives |
| US4434151A (en) | 1982-11-08 | 1984-02-28 | Medi-Physics, Inc. | Bifunctional chelating agents |
| US4673562A (en) | 1983-08-19 | 1987-06-16 | The Children's Medical Center Corporation | Bisamide bisthiol compounds useful for making technetium radiodiagnostic renal agents |
| US4746505A (en) | 1985-04-26 | 1988-05-24 | President And Fellows Of Harvard College | Technetium radiodiagnostic fatty acids derived from bisamide bisthiol ligands |
| US5122361A (en) | 1989-04-17 | 1992-06-16 | Trustees Of The University Of Pennsylvania | Dopamine receptor ligands and imaging agents |
| US5380848A (en) | 1990-08-09 | 1995-01-10 | Research Triangle Institute | Cocaine receptor binding ligands |
| US5496953A (en) | 1990-08-09 | 1996-03-05 | Research Triangle Institute | Cocaine receptor binding ligands |
| US5128118A (en) | 1990-08-09 | 1992-07-07 | Research Triangle Institute | Cocaine receptor binding ligands |
| WO1993009814A1 (fr) | 1991-11-15 | 1993-05-27 | Research Triangle Institute | Ligands de liaison de recepteur de cocaine |
| US5310912A (en) | 1992-02-25 | 1994-05-10 | Research Biochemicals Limited Partnership | Iodinated neuroprobe for mapping monoamine reuptake sites |
| US5262428A (en) | 1992-03-13 | 1993-11-16 | Wake Forest University | Biologically active tropane derivatives |
| US5760055A (en) | 1992-03-13 | 1998-06-02 | Wake Forest University | Biologically active tropane derivatives |
| JP2906085B2 (ja) * | 1993-05-18 | 1999-06-14 | ウエイク フォリスト ユニヴァーシティ | 生物学的活性トロパン誘導体による治療方法 |
| US5493026A (en) | 1993-10-25 | 1996-02-20 | Organix, Inc. | Substituted 2-carboxyalkyl-3-(fluorophenyl)-8-(3-halopropen-2-yl) nortropanes and their use as imaging for agents for neurodegenerative disorders |
| US6241963B1 (en) * | 1995-10-19 | 2001-06-05 | The Trustees Of The University Of Pennsylvania | Dopamine and serotonin transporter ligands and imaging agents |
| US5948933A (en) * | 1997-07-11 | 1999-09-07 | Organix, Inc. | Tropane analogs and methods for inhibition of monoamine transport |
| US6171576B1 (en) * | 1995-11-03 | 2001-01-09 | Organix Inc. | Dopamine transporter imaging agent |
| US7105678B2 (en) * | 1995-11-03 | 2006-09-12 | Organix, Inc. | Boat tropanes |
| US5700446A (en) * | 1996-06-13 | 1997-12-23 | Neuro Imaging Technologies, Llc | Synthesis of ferrocenyl phenyltropane analogs and their radio-transformation to technetium neuroprobes for mapping monoamine reuptake sites |
| WO1998024788A1 (fr) * | 1996-12-02 | 1998-06-11 | Georgetown University | Derives tropane et procede de synthese |
| US6358492B1 (en) | 1997-10-07 | 2002-03-19 | Research Triangle Institute | Dopamine transporter imaging ligand |
| AU763463B2 (en) * | 1998-09-23 | 2003-07-24 | Takeda Gmbh | Tetrahydropyridoethers |
| CA2285516C (fr) * | 1999-05-12 | 2010-12-07 | President And Fellows Of Harvard College | Agents d'imagerie pour transporteur de dopamine |
-
1999
- 1999-10-01 CA CA2285516A patent/CA2285516C/fr not_active Expired - Fee Related
- 1999-10-01 CA CA2721484A patent/CA2721484A1/fr not_active Abandoned
- 1999-10-20 IL IL13248899A patent/IL132488A0/xx unknown
- 1999-10-21 EP EP02006707A patent/EP1238978A3/fr not_active Withdrawn
- 1999-10-21 EP EP04026679A patent/EP1518561A3/fr not_active Withdrawn
- 1999-10-21 EP EP99121068A patent/EP1051980B1/fr not_active Expired - Lifetime
- 1999-10-21 DE DE29923477U patent/DE29923477U1/de not_active Expired - Lifetime
- 1999-10-21 DE DE69943038T patent/DE69943038D1/de not_active Expired - Lifetime
- 1999-10-21 EP EP04026685A patent/EP1518562A3/fr not_active Withdrawn
- 1999-10-28 KR KR1019990047098A patent/KR20000075416A/ko not_active Application Discontinuation
- 1999-10-29 GB GB9925630A patent/GB2349882B/en not_active Expired - Fee Related
- 1999-10-29 JP JP30959999A patent/JP5001480B2/ja not_active Expired - Fee Related
- 1999-10-29 AU AU57162/99A patent/AU783860B2/en not_active Ceased
-
2000
- 2000-05-10 US US09/568,106 patent/US6548041B1/en not_active Expired - Fee Related
-
2002
- 2002-04-02 JP JP2002100578A patent/JP2002338569A/ja active Pending
-
2006
- 2006-03-16 AU AU2006201099A patent/AU2006201099A1/en not_active Abandoned
- 2006-09-08 US US11/517,676 patent/US20070009432A1/en not_active Abandoned
-
2012
- 2012-01-05 JP JP2012000560A patent/JP2012067135A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| KR20000075416A (ko) | 2000-12-15 |
| CA2285516A1 (fr) | 2000-11-12 |
| GB2349882A (en) | 2000-11-15 |
| EP1051980A2 (fr) | 2000-11-15 |
| GB9925630D0 (en) | 1999-12-29 |
| JP2012067135A (ja) | 2012-04-05 |
| EP1051980A3 (fr) | 2002-05-22 |
| JP5001480B2 (ja) | 2012-08-15 |
| AU2006201099A1 (en) | 2006-04-13 |
| DE29923477U1 (de) | 2001-03-29 |
| US6548041B1 (en) | 2003-04-15 |
| AU783860B2 (en) | 2005-12-15 |
| EP1518561A2 (fr) | 2005-03-30 |
| JP2002338569A (ja) | 2002-11-27 |
| IL132488A0 (en) | 2001-03-19 |
| DE69943038D1 (de) | 2011-01-27 |
| CA2721484A1 (fr) | 2000-11-12 |
| EP1518561A3 (fr) | 2005-04-06 |
| EP1238978A2 (fr) | 2002-09-11 |
| US20070009432A1 (en) | 2007-01-11 |
| JP2000319201A (ja) | 2000-11-21 |
| EP1518562A2 (fr) | 2005-03-30 |
| AU5716299A (en) | 2000-11-16 |
| EP1238978A3 (fr) | 2005-03-02 |
| GB2349882B (en) | 2004-08-11 |
| EP1051980B1 (fr) | 2010-12-15 |
| EP1518562A3 (fr) | 2005-04-06 |
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